Premium
Ring opening reaction of the pyridinium salt of 4‐nitro‐3‐isoxazolin‐5‐one: A preparation of trifunctionalized methane derivatives
Author(s) -
Nishiwaki Nagatoshi,
Takada Yuji,
Inoue Yoji,
Tohda Yasuo,
Ariga Masahiro
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320215
Subject(s) - chemistry , pyridinium , nitro , ring (chemistry) , salt (chemistry) , cleavage (geology) , carbon atom , methane , medicinal chemistry , organic chemistry , alkyl , geotechnical engineering , fracture (geology) , engineering
The ring cleavage of the pyridinium salt of 4‐nitro‐3‐isoxazolin‐5‐one 1 was found to proceed under mild basic conditions and to give cyano‐ aci ‐nitroacetates 2 in quantitative yields. The ring opened products 2 have three different functional groups at the same carbon atom, and are worth applying as a useful building block to syntheses of polyfunctionalized compounds.